Vat dyestuffs of the benzanthronylaminoanthraquinone series



Patented Sept. 27, 1938 UNITED STATES PATENT OFFICE VAT DYESTUFFS OF THE BENZANTHRO- SERIES Ernst Honold, Frankfort-on the-Main-Fechenheim, Germany, assignor to General Aniline Works, Inc., New York, N. Y., a corporation of Delaware No Drawing. I Original application July 15, 1936,

Serial "No. 90,1730. Divided and this application November 13,1937, Serial No. 174,353. In

Germany July 17, 1935 4 Claims. (Cl. 260-274) This application is a division of my application Serial No. 90,730, filed July 15, 1936, which relates to vat dyestufls of the benzanthron'ylaminoanthraquinone series. 1

densation products wherein X stands for a member selected from the group consisting of NH2 and N02, on alkaline conof bzl-benzanthronyl-laminoanthraquinones of the general formula:

v H O N My present invention relates to new vat dye stufis of the benzanthronylaminoanthraquinone series, more particularly those of the generaliormula:

H o N O n NH o COOl wherein Z stands for a memberselected from the group consisting of NH2.

'I"h en1 zw"dyestuffs thus obtained dyethe vegetable, i brejbrownish violet shades of very good u: fastness.- properties. They are especially valuable products onaccount of the red color component contained in the shadesobtained there with, since it is impossible to obtain violet shades with the samegood 'fastness properties by means of analogous dyestuffs which do not contain a radicle of the anthraquinone 2-carboxy1ic acid of "the above said general formula.

In order to further illustrate my invention the following examples are given, the parts being by weight and all temperatures in degrees centigrade.

Example 1 66 parts of the condensation product of the formula:

H o N- NE I ll NH2 0 are suspended in about 600 parts of ortho-dichlorobenzene. Then, at about 35 parts of 1-nitroanthraquinone-2-carboxylic acid chloride are slowly added and the mixture is heated to boiling for some hours while stirring.

The new dyestuff thus obtained of the general formula:

dissolves in concentrated sulfuric acid with a green color and dyes cotton from a dark brown vat very fast brownish violet shades. v

The aforesaid starting material may be obtained by the action of caustic alkali on the product obtainable by consecutive condensation of bzl-6dibromobenzanthrone with one molecular proportion of 1-amino-5-benzoylaminoanthraquinone and of l-aminoanthraquin'one, the

benzoyl group being split off by saponification. This initial material dyes cotton from a brownish black vat grey shades which are not fast to chlorine.

Example 2 53 parts of the condensation product of the formula are suspended in a finely divided form in about 600 parts of ortho-dichlorobenzene. Then 35 parts of l-nitro-anthraquinone-2-carboxylic acid chloride are slowly added and the mixture is heated to boiling for some hours in an apparatus provided with a stirrer and a reflux condenser. The dyestuff thus obtained of the formula:

is distinguished by a good solubility in the vat and by a good levelling power. It dissolves in concentrated sulfuric acid with a green color and dyes cotton from a blackish vat fast violet shades.

Identical dyeings are obtained by employing the analogous dyestufi which is obtained by condensing 1-aminoanthraquinone-2-carboxylic acid chloride with the above described initial ma- I claim: 2. The vat dyestuflz' of the formula:

l 0 15 d which dyestuflf dissolves in concentrated sulfuric 1. Vat dyestuffs of the benzanthronylaminoacid with a green color and dyes cotton from a anthraquinone series of the general formula: dark brown vat very fast brownish violet shades.

I 25 3 x IIIH wherein X stands for a member selected from 3. The vat dyestuif of the formula:

. 40 NH 0 0 N0;

0 the group consisting of NH2 and N02 and wherewhich dyestuff dissolves in concentrated .sul- 50 in Y stands for a member selected from the group furic acid with a green color and dyes cotton consisting of hydrogen and an anthraquinone-2- carboxylic acid amide radicle substituted in the from a black vat very fast violet shades.

4. The vat dyestuff ofthe formula:

l-position by the radicle X which has the above which dyestufi dissolves in concentrated sulfuric said signification, which dyestuffs dye the vegeacid with a green color and dyes cotton from a table fiber brownish violet shades of very good black vat very fast violet shades. fastness properties.

ERNST HONOLD. 

